Woodstock Rentals

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Reading Farms Estate/ Vermont Luxury Rental

Reading villa

  • 15 bedrooms
  • 12 bathrooms
  • sleeps 46

Price per night from

$5,096

Cozy Historic Hilltop Cottage

Brownsville house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$212

Village Farmhouse - mins to GMHA, Okemo, Killington. Pet-friendly.

Reading house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

Price per night from

$287

NEW! Luxe Lodge with Best Views, near Silver Lake+Woodstock

Barnard house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$395

Farmhouse Rustic Lux on 10 acres w/ swimming pond

Bridgewater house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 22

Price per night from

$745

Private, peaceful home

South Pomfret house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$802

Chase House Inn - Edwin Stanton Room

Cornish house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$172

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About Woodstock

With numerous options for outdoor recreational activities, interesting historical sites, and friendly locals, the Vermont town of Woodstock has it all! Central Street is the primary commercial shopping district in Woodstock, but you can also visit The Green for some of the best restaurants that the state has to offer.

Here are a few additional suggestions of things to do in Woodstock:

  • Billings Farm and Museum: Visit this 270 acre farm, dairy barn, and museum with historic artifacts.
  • Ottaquechee River: This river that runs through Woodstock offers plenty of opportunities for fishing and canoeing excursions.
  • Dana House: This small museum hosts several pieces of artwork and historic artifacts from the local area in the 19th century.
  • Mount Tom: Climb to the top of Woodstock's main mountain for stunning views of the town and surrounding areas.

There are many events and festivals held throughout the year in Woodstock that bring the whole community together. Watch the parade through town featuring horses and costumed riders during Wassail weekend in February, sample artwork from the top painters and sculptors in the region during the Woodstock Art Festival in September, or try the local cuisine from the best chefs and brewers in the state during the Taste of Woodstock event in September.

To get the most out of your time in Woodstock, stay in a vacation rental. Rent a villa or condo close to the historic sites throughout town, or book a cozy cabin with amazing mountain views right outside your door.

If you wish to explore the rest of the region, Woodstock is only a short drive from some of the other popular towns and cities in Vermont. The hiking options found in Rutland and the colonial village of Barre can both be reached within an hour by car.

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